Sodium Bicarbonate → (3beta,20R)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol

HRID 1385615Notes

Reaction equation

HRID 1385615 reaction equation
[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:19])[CH3:18])[CH2:8]1)[CH3:5])[CH3:2].C(=O)([O-])O.[Na+]>C(O)CCC>[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([OH:19])[CH3:18])[CH2:8]1)[CH3:5])[CH3:2].[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@@H:17]([OH:19])[CH3:18])[CH2:8]1)[CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 54547839(3beta)-3-[(1-Ethoxyethyl)oxy]pregn-5-en-20-one

Product 2

HCID 54499379(3beta,20R)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-olHCID 54499381(3beta,20S)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

—Sodium (8.98 g) was added in small portions in the course of 2 h to a refluxing solution of (3β)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-one (20 g) in dry n-butanol (587 ml). Heating was continued for another 2 h; then the reaction mixture was cooled and poured into a saturated aqueous solution of sodium hydrogen carbonate (1.5 l). The product was extracted into ethyl acetate; the combined organic phases were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Column chromatography of the crude product afforded (3β,20R)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol (5.08 g) and (3β,20S)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol (compound 3, 7.21 g).

Workup

  1. temperatureHeating
  2. temperaturethen the reaction mixture was cooled
  3. extractionThe product was extracted into ethyl acetate
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-857bb3e2f3d84941b89ffecb26dcee83
Source dataset
uspto-grants-2001_07
Patent number
US06262282B1

Reaction notes

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